4-Hydroxy-4-ethyl-hexin-(2)-saeure-(1)-ethylester | 70404-17-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-Hydroxy-4-ethyl-hexin-(2)-saeure-(1)-ethylester
• 英文别名: ethyl 4-ethyl-4-hydroxyhex-2-ynoate；4-Ethyl-4-hydroxy-2-hexinsaeureethylester
• CAS: 70404-17-0
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: GALXJQSLBPIXIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-4-ethyl-hexin-(2)-saeure-(1)-ethylester 在 ammonium hydroxide 作用下， 生成 4-Hydroxy-4-ethyl-hexin-(2)-saeure-(1)-amid
  参考文献：
  名称：

  Notes- Potassium Hydroxide as a Catalyst for the Condensation of Propiolic Acid or Propiolic Esters with Ketones

  摘要：

  DOI：

  10.1021/jo01078a605
• 作为产物：
  描述：

  乙醇 、 4-Hydroxy-4-ethyl-hexin-(2)-saeure-(1) 在 硫酸 作用下， 生成 4-Hydroxy-4-ethyl-hexin-(2)-saeure-(1)-ethylester
  参考文献：
  名称：

  Notes- Potassium Hydroxide as a Catalyst for the Condensation of Propiolic Acid or Propiolic Esters with Ketones

  摘要：

  DOI：

  10.1021/jo01078a605

文献信息

• Cobalt‐Catalyzed Regioselective [4+2] Annulation/Lactonization of Benzamides with 4‐Hydroxy‐2‐Alkynoates under Aerobic Conditions
  作者：Nachimuthu Muniraj、Anil Kumar、Kandikere Ramaiah Prabhu

  DOI：10.1002/adsc.201901119

  日期：2020.1.7

  A cobalt‐catalyzed regioselective [4+2] annulation/lactonization reaction of benzamides with 4‐hydroxy‐2‐alkynoates is reported. This reaction utilizes air as an oxidant rather than metal salts. The method is operationally simple, mild, and sustainable. This protocol exhibits a broad substrate scope and compatible with a variety of functional groups furnishing the corresponding 1,4‐dihydrofuro[3,4‐c]isoquinoline‐3

  据报道，苯甲酰胺与4-羟基-2-链烷酸酯发生钴催化的区域选择性[4 + 2]环化/内酯化反应。该反应利用空气而不是金属盐作为氧化剂。该方法操作简单，温和且可持续。该方案具有广泛的底物范围，并与提供相应的1,4-二氢呋喃[3,4- c ]异喹啉-3,5-二酮衍生物的各种官能团兼容，具有良好的产率和较高的区域选择性。
• Manganese‐Catalysed C−H Activation: A Regioselective C−H Alkenylation of Indoles and other (hetero)aromatics with 4‐Hydroxy‐2‐Alkynoates Leading to Concomitant Lactonization
  作者：Anil Kumar、Nachimuthu Muniraj、Kandikere Ramaiah Prabhu

  DOI：10.1002/adsc.201900678

  日期：2019.11.5

  A manganese‐catalyzed C−H bond alkenylation of indoles at C2‐position with 4‐hydroxy‐2‐alkynoates leading to concomitant lactonization under removable directing group strategy has been disclosed. This lactonization strategy exhibits regioselectivity, a broad substrate scope, and a good functional group tolerance furnishing the products in low to high yields. The regioselectivity is guided by the electronic

  已经公开了锰在4-位-2-羟基的链烷酸酯在C2-位的吲哚的锰催化的CH键链烯基化，从而在可移动的导向基团策略下导致伴随的内酯化。这种内酯化策略显示出区域选择性，广泛的底物范围和良好的官能团耐受性，从而以低到高收率提供了产品。区域选择性受酯基团的电子效应以及4-羟基-2-链烷酸酯的C4位的空间体积的影响。反应后，直接除去了导向基团以获得不含NH的吲哚。
• Synthesis of Furanone-Fused 1,2-Benzothiazine by Rh(III)-Catalyzed C–H Activation: Regioselective Oxidative Annulation Leading to in Situ Lactonization in One Pot
  作者：Vinayak Hanchate、Anil Kumar、Kandikere Ramaiah Prabhu

  DOI：10.1021/acs.joc.9b01899

  日期：2019.9.6

  sulfoximine-directed C–H activation strategy catalyzed by a Rh(III)-catalyst leads to an efficient synthesis of furanone-fused 1,2-benzothiazine. In this reaction, cascade C–H activation, regioselective annulation, and lactonization occur in one pot. 4-Hydroxy-2-alkynoates, as coupling partners, form unsymmetrical alkynes, which undergo lactonization after C–H activation and regioselective annulation. The

  由Rh（III）催化剂催化的由亚砜亚胺指示的CH活化策略可有效合成呋喃酮熔合的1,2-苯并噻嗪。在该反应中，一锅中发生级联的C–H活化，区域选择性环化和内酯化。4-羟基-2-炔酸酯作为偶联伙伴，形成不对称炔烃，在C–H活化和区域选择性环化反应后发生内酯化。该方法显示出良好的范围，具有广泛范围的亚砜亚胺和炔酸，并在以高收率形成单一区域异构体时显示区域选择性。
• Rhodium(III)-Catalyzed C–H Activation: A Cascade Approach for the Regioselective Synthesis of Fused Heterocyclic Lactone Scaffolds
  作者：Anil Kumar、Kandikere Ramaiah Prabhu

  DOI：10.1021/acs.joc.9b03266

  日期：2020.3.6

  A Rh(III)-catalyzed cascade C-H activation; regioselective [4 + 2] oxidative annulation; and lactonization of aromatic acids, anhydrides, and acrylic acid derivatives with 4-hydroxy-2-alkynoates have been disclosed. This strategy leads to fused heterocyclic lactone scaffolds in a single step with moderate functional group tolerance and excellent site selectivity. Besides, in one step, an antipode of

  Rh（III）催化的级联CH活化；区域选择性[4 + 2]氧化环化；已经公开了芳族酸，酸酐和丙烯酸衍生物与4-羟基-2-链烷酸酯的内酯化反应。这种策略可以一步合成具有稠合的杂环内酯支架，具有中等的官能团耐受性和出色的位点选择性。此外，一步合成了含有三环异香豆素骨架的头孢菌中间体天然产物的对映体。
• Synthesis of Naphthols by Rh(III)-Catalyzed Domino C–H Activation, Annulation, and Lactonization Using Sulfoxonium Ylide as a Traceless Directing Group
  作者：Vinayak Hanchate、Anil Kumar、Kandikere Ramaiah Prabhu

  DOI：10.1021/acs.orglett.9b03182

  日期：2019.10.18

  Sulfoxonium ylide directed C–H activation catalyzed by the Rh(III)-catalyst has been disclosed. In this study, sulfoxonium ylide functions as a traceless directing group, which reacts with an unsymmetrical alkyne, 4-hydroxy-2-alkynoate, to form the corresponding furanone-fused 1-naphthols. The application of the methodology has been illustrated by synthesizing bromo lactones, which are used as an intermediate

  已公开了由Rh（III）催化剂催化的磺化on叶立德对C–H的活化作用。在这项研究中，次硫酸sulf叶立德起着无痕导向基团的作用，它与不对称炔烃4-羟基-2-炔酸酯反应形成相应的呋喃酮稠合的1-萘酚。通过合成溴内酯来说明该方法的应用，溴内酯是合成光致变色二色性材料的中间体。我们还证明了纤维y内酯A类似物的合成。